Holiday rentals in Deer Isle

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Top-rated holiday rentals in Deer Isle

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Guest favourite

Home in Stonington

4.9 out of 5 average rating, 125 reviews

Puppa’s View- a private waterfront home

The perfect vacation property. Private and comfortable 2 bedroom ocean front home with sweeping views of Allen Cove and Penobscot Bay. Just 1 mile from the bustling Stonington Village and a quick drive to anywhere on Deer Isle. The home has dedicated workspaces in each bedroom, a gigantic, fully-equipped kitchen and is spacious and peaceful. Wake to breathtaking sunrise views and find yourself stopping to appreciate the sunset over this quiet cove. I will happily help customize your itineary.

20–27 Jan

$420 SGD per night

Guest favourite

Cottage in Sedgwick

4.99 out of 5 average rating, 188 reviews

Exquisitely Modern Maine Cottage @Diagonair

Private getaway cottage is a favorite of honeymooners & lovers of modern design. * 2,000 square foot modern cottage on 12 acres of woods and fields * One hour to Acadia National Park & Bar Harbor; 15 min to shopping, hiking, swimming * 2 full baths, one with a steam shower * Fully equipped kitchen with Wolf stove and under-counter Sub-Zero fridge * Two gas fireplaces, one indoors, one on a covered deck (*NEW*) * Queen bed with luxurious linens and pillows * Smart TV; gas grill * EV charger

30 Apr – 7 May

$650 SGD per night

Guest favourite

Tiny home in Stonington

4.91 out of 5 average rating, 247 reviews

Island Getaway - Modern Tiny House Coastal Retreat

★ You will be walking distance from downtown Stonington where you can enjoy local shops, artwork and immerse yourself in the island community. Our tiny home was constructed with high quality materials that are locally sourced and includes a mini split heat pump, full kitchen, walnut countertops and custom hardwood self-close cabinets. Modern yet cozy and situated in picturesque Stonington with a faint view of the harbor. ★ Complementary Kayaks Rentals when you stay 3 nights or more! ★

9–16 Oct

$296 SGD per night

Guest favourite

Guest house in Lincolnville

4.97 out of 5 average rating, 327 reviews

"The Lair" Guesthouse

"The Lair" is a just recently renovated small 200 square foot cabin with vaulted ceilings and plenty of natural sunlight. The building is located close to Green Tree Coffee and Tea, a coffee roaster, so the aroma of coffee will be in the air. We located about 400 yards South of the Islesboro Ferry and Lincolnville Beach and 2.4 milres North of Camden Hills State Park and Mount Battie. Free coffee and tea everyday, all day! We are closed for Winter, will re-open Mid-April. Thank you.

16–23 May

$185 SGD per night

Guest favourite

Guest house in Orland

4.99 out of 5 average rating, 103 reviews

Cozy cottage in Orland Village-Penobscot Bay area

Charming cottage in Orland Village, 2 minutes from Bucksport, a short walk away from the Orland River and its estuary on the Penobscot Bay. Nestled on 3.5 acres of wooded land, 300 ft behind an 18th-century colonial house. Completely self-contained with equipped kitchen. Fast 400 Mbs cable internet/WiFi. 45 minutes to Acadia National Park, 30 min. to Belfast, 20 min. to Castine. Perfect base for hiking, kayaking, sailing, or discovering the maritime past of the area. Pet friendly!

17–24 Jan

$134 SGD per night

Guest favourite

Tiny home in Blue Hill

4.94 out of 5 average rating, 155 reviews

New enchanting retreat near Acadia National

The camp is brand new on 27 acres of land 3 min to Blue Hill Mountain and 5 min to Blue Hill downtown which is right on the water of The Blue Hill Bay. This is an edge wood enchanting retreat perfect for two to hear birds, squirrels and porcupines. Remember to pick some blueberries when it is in season before the black baby bear down the road eat them all. 3D nature is unfolding right in front of your eyes and Acadia National Park is 50 min drive from here. Oh man, you are free! 编辑

5–12 Sep

$193 SGD per night

Guest favourite

Cottage in Deer Isle

4.9 out of 5 average rating, 115 reviews

The Sailors Retreat - Waterfront Home with Kayaks!

Retreat to this coastal Maine getaway just steps away from your own private ocean and beach front while roasting marshmallows by the bonfire enjoying the amazing view and a short drive to Acadia National Park. Spend the day exploring tidal pools, relaxing in the sun, kayaking, enjoying some Maine Lobster or take it easy and just enjoy a cup of coffee while taking in the spectacular views and listening to seagulls and waves crashing; Something to do for all members of the family.

15–22 Jan

$287 SGD per night

Guest favourite

Cottage in Deer Isle

4.94 out of 5 average rating, 282 reviews

Beachfront Guest Cottage - Year-round Hot Tub!

Our cozy guest cottage has easy beachfront/kayak/canoe access, and is located very close (within walking distance at low tide) to the public boat launch for larger boats. Great location to explore Deer Isle, Acadia (approx 1hr), Castine (45m), and the Bangor (1hr) area. Brave children and adults even swim from the beach but comfortable swimming ponds/lakes are 10m in several directions. The hot-tub is open year-round! Additional guests can be considered prior to booking.

21–28 Oct

$284 SGD per night

Guest favourite

Guest house in Sedgwick

4.96 out of 5 average rating, 235 reviews

Tiny house with AC!!

A tiny guest house (450 sq ft) overlooking the Benjamin River. AC!!. Enjoy a cup of coffee on your private porch. Living area has a smart tv (no cable, but internet available to access your streaming account). DVD's also available. Kitchenette comes with Keurig with k-cups included, mini fridge, coffee maker/filters, toaster oven, microwave, 2 burner hot plate (no oven), dishes/pots and pans. There is a loft with an army cot. Not suitable for children under age 5.

26 Feb – 5 Mar

$190 SGD per night

Guest favourite

Tiny home in Blue Hill

4.84 out of 5 average rating, 132 reviews

Mini Moose Tiny Home

Our Mini Moose sits on our 65 + acres of beautiful Maine woods. Two miles from the center of the coastal village of Blue Hill. Five years of rentals. Fire pit & view of the pond from the deck. 2 paths around 2 ponds, swimming is allowed and a contemplative walking labyrinth. Perfect getaway for a couple or single person to explore the natural beauty of Downeast Maine. Only 45 minute drive to Acadia National Park and close to all that Downeast Maine has to offer.

25 Aug – 1 Sep

$133 SGD per night

Guest favourite

Cottage in Brooklin

4.98 out of 5 average rating, 178 reviews

Historic School House now with High Speed Internet

Historic schoolhouse of Brooklin converted into the perfect one bedroom getaway. Located across the street from the Brooklin Rockbound Capel with a quick 20-minute drive to Blue Hill. Acadia National Park, Bar Harbor or Bangor are all with in an hour away. The original post and beam construction, with a sleeping loft, give the interior a rustic vibe offset by the playful color palette and butterfly wallpaper make it more botanical and lighthearted.

11–18 Oct

$244 SGD per night

Superhost

Cottage in Deer Isle

4.88 out of 5 average rating, 41 reviews

Cozy complete camp on cove Perfect for couple

Everything you need for a real Maine stay. Downstairs incudes kitchen area and bathroom (with unlimited hot water!). Double bed in upstairs loft, sun porch offers additional sleeping area. Picnic table and fire pit at cove’s edge with beautiful views. Fresh water pond for swimming in village. 15 minutes from Stonington, day trip to Acadia, fresh lobster around the corner and close to Nervous Nellie’s Jams and Jellies. Must be seen to be believed.

18–25 Dec

$144 SGD per night